Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (E)-Ethyl 3-(6-chloro-4-(methylamino)pyridin-3-yl)acrylate

HRID 710579

Reaction equation

HRID 710579 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=O)=[C:4]([NH:10][CH3:11])[CH:3]=1.[C:12]([CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:14][CH2:15][CH3:16])=[O:13]>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:17]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:4]([NH:10][CH3:11])[CH:3]=1

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 234345716-Chloro-4-(methylamino)nicotinaldehyde

Product 1

HCID 86686188(E)-Ethyl 3-(6-chloro-4-(methylamino)pyridin-3-yl)acrylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-chloro-4-(methylamino)pyridine-3-carboxaldehyde (3.41 g, 20 mmol) in THF (120 mL) was added (carbethoxymethylene)triphenylphosphorane (8.35 g, 24 mmol). The mixture was heated at reflux for 16 h, and was then cooled and concentrated. The residue was chromatographed on silica gel (12% ethyl acetate in hexanes eluant) to provide the title compound. MS (m/z) 241.0 (M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. temperaturewas then cooled
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel (12% ethyl acetate in hexanes eluant)

Sources & evidence

ORD record
ord-a484fae59d4b4f3397004f0e33a035de
Source dataset
uspto-grants-2015_11
Patent number
US09181238B2

Linked notes

Loading…